Catechuic acid and ethyl 2,4,5-trihydroxybenzoate from D-glucose

Bhujbal, Namdeo N. ; Bande, Omprakash P. ; Dhavale, Dilip D. (2009) Catechuic acid and ethyl 2,4,5-trihydroxybenzoate from D-glucose Carbohydrate Research, 344 (6). pp. 734-738. ISSN 0008-6215

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Synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived β-ketoester is described. The polyhydroxylated β-ketoester obtained from the hydrolysis of sugar β-ketoester 3 was subjected to an aldol-type condensation to get 4 that on enolization, dehydration, and hydrogenation afforded ethyl 2,4,5-trihydroxybenzoate (2). On the other hand, hydrogenation of aldol product 4 afforded polyhydroxylated keto-carbasugar 6, which on mild acid treatment and ester hydrolysis in basic media led to catechuic acid 1. Intermediate 4 is co-related to 3-dehydroshikimic acid, a biochemical intermediate from D-glucose in the synthesis of pro-catechuic acid.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Aldol Reaction; β-ketoester; Carbocycles; Carbohydrates; Phenolic Acids
ID Code:9662
Deposited On:02 Nov 2010 11:12
Last Modified:31 May 2011 11:49

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